A Virgin Hitchhier

The weather in this part of the country sucks. I was born and raised here and never quite got used to temperatures in the low hundreds in the summer and then howling winds that blew the snow parallel with the ground all winter. This wasn't Minnesota or one of those states but Kansas. Yeah, the home of wheat and coyotes.

I'm Bob and twenty-seven and was on my way from Wichita to just south of San Antonio, Texas for a job interview and was tooling along just over the Oklahoma line at seventy when I saw a young fellow at the side of the road with his thumb out. I pulled over and he ran up to my passengers' door; he was wearing a backpack and carrying a small suitcase so perhaps I should say he waddled up.

"Hi, I'm going down into Texas. Are you heading that way?"

"Sure am tiger, hop in."

The young fellow looked to be totally dehydrated with the Kansas heat and I asked if he would like a drink. I had a cooler in the back of the van with some beer, soda and water on top of a couple of bag of ice. In this kind of weather I never leave home without being prepared. Any breakdown along some of the lightly traveled highways out here can be deadly without readily available liquids. He almost jumped into the rear seat to get a soda.

I was just cruising along and our conversations ranged from sports, to current events and then all around the gym in politics. He introduced himself as Jimmy and was nineteen and was going to Texas to see an old friend of his from school.

"Jimmy, I'm planning on stopping at the next rest stop and going in for a sandwich or something. I'll be more than happy to pay for yours if you would like to join me."

"Gee, that would be great. I didn't have any breakfast and I'm almost broke and starving."

Our late lunch early dinner hit the spot. I hadn't had any lunch and only toast and coffee for breakfast so my stomach was talking to me.

By the time we were back in the van and heading south we were at ease with each other and our conversation was far more interesting. I pushed him on his love life and he sadly told me his girlfriend had dumped him for another guy some months ago and he hadn't found anyone else since. He was quite open about his sex with her and figured that might have been the reason for the breakup. He moaned that he wasn't very well hung and he thought her old boyfriend was so that was why she went back with him.

"Jimmy, open the glove compartment and grab that yellow envelope. There are some pictures there that might give you some satisfaction."

The pics were of nudes of various descriptions. There were some of just gals, others of guys and gals in action, and some of guys in action with other guys.

He thumbed through them somewhat fast but then went back over them paying a lot more attention to each pic the second time through them.

"Holy shit, look at the tits on her" he howled as he came across one particularly well endowed.

He was starting to spend more time on each pic and I noticed that he was spending a fair amount of time on the gay male shots as well.

I'm bisexual and looking down at his crotch could see a slight bulge that could be interesting.

He kept going back to the beginning of the pile and then starting over again. By his second or third time through them I could actually hear him breathing a little harder. At one point he reached down to his crotch to reposition his cock. It must have been getting a little harder and was cramped for space the way it was positioned. Damn, he wasn't going to be with me forever so if I was going to have something happen with him it would have to start soon.

"Jimmy, from the bulge growing in your jeans it looks as if some of them are getting you a little excited." I joked.

"Yeah, some of them are hotter than any I have ever seen in real life" he answered.

"Why don't you let that thing out for some air before it gets strangled in your pants?" I said as I reached over and lightly rested my hand on his bulge.

He just looked at me and sort of stuttered, "Maybe I ought to. It's starting to hurt it's so cramped up in these tight jeans."

"Here let me help." As I moved my fingers to the top of his zipper and started to lower it.

He moved his hand under mine and lowered the zipper to the bottom. I looked over and when I saw that I let my fingers delve inside and freed up his cock to come out. He was right, he was a little on the small side and it was obvious why his girlfriend left..

Fortunately the traffic was very light so I didn't have to worry about that as my fingers started to lightly massage the head of his cock. He had been circumcised so my fingers instantly went to the head of it and gathered some of his precum and rolled it around.

"Oh God Bob, that feels wonderful. I never had a guy do this for me before."

"Just lay your head back against the head rest and relax and let me give you some relief."

A few miles further down the road there was a parking area and I pulled over and got in the shade of a few trees planted around the perimeter. As soon as I got the van parked I moved my seat back to give myself some room and then leaned over and positioned my head just above the head of his throbbing cock and slowly lowered my mouth to take it in. He had his eyes closed as I was doing this and I could feel him jump up with the shock of my warm mouth wrapped around the top of it.

"Oh Bob, do it, please do it. I never could talk my girlfriend into sucking me off."

I began to raise and lower my mouth. His cock was small enough I could easily take it all the way in without gagging. He was excited enough that I knew it wasn't going to be long before he was exploding. I let my free hand move down and lightly encircled his balls. As soon as I touched them he unloaded. A good few spurts of his hot come shot to the back of my throat as I continued moving and sucking. By that time he was squirming his ass around and trying to push his softening cock deeper in my mouth. I let my mouth remain just where it was as I licked up every drop of his come. Every time my tongue slid over the head of his cock he moaned some more. This fellow's cock has been seriously neglected.

I lifted my head and moved over and pulled his face to me and planted a huge kiss on his waiting mouth.

"Bob, you were wonderful"

"Glad you enjoyed it Jimmy," as I reached down and let my own cock out. Jimmy only had about four inches of hard cock and I certainly wasn't like any of the monsters talked about on in the online chat rooms but I did have a solid seven inches and it was harder than a rock right then.

"Jimmy, give me your hand and how about you letting it give me some pleasure?"

"You mean you want me to jack you off."

"Well, after what I just did for you ... yes."

"Bob, I never did that to a guy before. You won't think I am weird if I do it for you will you?"

"Hell no Jim. You are just a guy giving another guy some relief."

I moved his hand over the top of my shaft and he instantly wrapped his fingers around my shaft and began to go through the motions.

"Jimmy, hold on and let me lower my pants to give you some more room."

I dropped my jeans to my ankles and it was if he was mesmerized with looking at my cock. His eyes never left it and his hand quickly went back to where he had been holding it.

"Geez, you're huge." He mumbled.

I did every thing in my power not to have an orgasm too quickly for I wanted this young fellow to wrap his warm mouth around my cock before I came.

He was jerking a little too fast and I had him slow down and knew I could hold off a long time at the rate he settled in on. He moved around so his head was facing my cock closer than it was and he had one hand on my shaft and he let the other one roam around my balls and them up and onto the head of my now pulsing cock.

I moved a hand to the back of his neck and pulled down ever so gently.

"Jimmy, just let your lips touch the head of me and I'll come a lot faster."

"Geez Bob, I could never suck you off it that's want you want me to do."

"Just do as I ask and we'll see where it leads." I answered.

I continued with the slight pressure on the back of his neck and he did have his lips barely touching the very tip of my cock.

"Jimmy, open your mouth a little and let the very tip of my cock in a little ways."

He did that without any comment and as soon as I felt his mouth open I increased the pressure on the back of his neck and threw my hips up a little and ended up with a few inches buried in his hot virgin mouth.

He pulled away saying, " Bob, don't shoot in my mouth. It will make me sick."

"Jimmy, don't sweat it. I felt the exact same way the first time I did it too."

He put his mouth back down and was soon moving up and down exactly the same way I did to him just a few minutes earlier. I soon felt the pressure rising in my balls and knew I'd be coming in a few seconds. I then put both hands behind his head and pulled down on it at the same time I was throwing my cock up at him. I got another inch or two in before I began to unload. I shot stream after stream deep into his throat and I could hear as well as feel him gagging. I pulled out and told him to open the door on his side if he was going to be sick. I damn sure didn't want him puking all over my van.

"No, I'll be all right." He answered.

"Bob, that wasn't fair. You pulled me down on you so hard I couldn't get up at all. It felt as if you were going to jam your cock all the way down my throat."

"Jimmy, I'm sorry but you really did get me hot and I lost control for a few seconds there. You sure made me feel good. How many other guys have you done that to?" I asked thinking that I knew the answer but thought I'd give him a chance to change what I thought it was.

"Damnit Bob, that is the first time I ever did that and when you did it to me that was the first time for that too."

"Oh yeah, I'm sorry Jim, I forgot. Hey, get your mouth back down there and lick up the rest of my juices the way I did for you."

He dropped his mouth down and soon had his tongue encircling the head of my cock lapping up everything that was still showing. There was no question he was enjoying this and I knew that before this day was over he would be doing it again and possibly a lot more.

We sat like that for quite some time. I had one hand on his now soft cock and he was resting his on the head of mine.

"Jimmy, as I told you earlier I am heading to a spot just south of San Antonio and know that I'll never make it there today. I am thinking of getting a motel just outside of Dallas, grabbing some dinner and then hitting the sack and getting up early in the morning ready to finish the trip. You can stay with me if you want depending on how far you have to go."

"Hell Bob, I'm heading all the way down to the coast so I'll be happy to tag along with your plans. I'm sure I can get another ride in the morning down as far as I need to go."

Super news for that will give me a chance to see just how far I can take this sweet little virgin.

I was able to get a king size bed in the Quality Inn I checked into and we found a great steak house only a short walk away from it. I had a tasty T-bone and Jimmy settled for a Sirloin before we headed back to the room.

We weren't in the room for a few minutes when I told him to drop his pants and sit on the easy chair in the corner. He just looked at me but did exactly as I ordered.

"Jimmy, I'm going to give you a better blow job than you ever even dreamed of before now."

I stripped down as well and as soon as he sat on the chair I dropped between his legs and began to fondle his completely soft cock. It wasn't showing any sign of life when I raised up and planted a kiss on his sweet lips. "Oh Bob, that was the second time you kissed me and I never had a guy do that before."

"Jimmy, you must have enjoyed it because just look at your cock. It is standing up to its full length."

I dropped down and took his little shaft between a couple of fingers and then began to lick it from the base up to the tip and back again. He was small enough that I could get him completely in my mouth and have my face buried in his pubic hair. When I had him all the way in I used my tongue to lick under his shaft and that seemed to turn him on a little more. I then thought of trying something that would later turn out to be more interesting. I wet a finger and then dropped that hand down under his cheeks and let the wet finger play around with the puckered lips of his asshole. He moaned a little with that and when I slipped the finger in his ass up to the first knuckle he threw his ass from side to side saying, "Oh yes, Bob, that feels terrific." Well now, maybe better things are ahead.

I pushed that hand a little more and soon had the finger buried up to the middle knuckle and he was moaning big time. I then began to fuck his ass with the finger and he threw his arms wide open saying, "Oh God, that feels magnificent." It wasn't much longer before he was shooting his load down my throat again and I quickly licked up every drop.

I went into the bathroom to clean up and when I returned to the room he was sitting on the side of the bed with the remote control from the TV in his hands as he changed channels. My cock was hard anticipating what might be in store for it and I walked up to him and pushed my cock in his face and said,

"Your turn to do your thing Jim:

He was somewhat reluctant to make a move but I put one hand behind is head and guided him to where I wanted him. When my cock was in front of his mouth I pushed forward a little and I soon had it pushing against the lips of his sweet little mouth.

"Open up Jim and take care of me."

As soon as I felt his mouth open I pushed in and soon had it in about four inches. I didn't think he could take any more without gagging so I stopped there.

"Go to it Jimmy, move that sweet mouth of yours on me."

As he began to move on and off of me I reached behind his head with both hands and pulled him to me. I wasn't going to wait for him to get his motions down pat ... I was going to fuck his face until I exploded.

Every now and then I would push another inch in deeper and then pull out a bit before he got sick.

"Jimmy, use your tongue while it's in your mouth, let it roam all around me."

It didn't take long before I was filling his mouth with my come.

"Jimmy, c'mon, lick me clean and swallow every drop."

Did he ever. By the time his mouth was finished cleaning me off there wasn't a drop of my juices anywhere to be seen.

He pulled off and looked up at me and asked,

"Bob, did I do it right for you? I sure wanted to make you feel good."

"You were perfect Jimmy. You seem to be getting better at it each time you do it for me."

After the excitement he showed when I had my finger up his ass earlier I had some intentions of introducing my cock to it but was a little fearful it would scare him off. It might be better to take it easy and arrange to do that another time.

Just then he looked up at me and said,

"Bob, there is something about me that I didn't tell you about."

"And what's that."

"I won't be returning to my home up in Wichita. My father died a few years back in a car accident and my mother has been going from one guy to the next for that last year or so. A few months ago she announced she was going to marry her current boyfriend and they were going to sell our house and move into a one-bedroom apartment so I would have to find my own place to live. That's the reason I am going down to see my old friend hoping he'll let me live with him. Another thing is that when you kissed me earlier that was the first time in as long as I can remember anyone showed any feeling for me at all. I could have cried when you did it."

Oh shit, this could get serious in a hurry.

"Well, I'm sorry to hear about your mother's decision but I am happy that I was the one who showed you some love and feelings. Come up here and let me give you a hug."

He almost jumped into my arms and I lowered him to the bed.

"Tiger, its about time we got some shut eye if we are going to get on the road at a reasonable time in the morning."

"OK Bob and he flung himself over to the far side of the big bed.

It must have been four or five in the morning when I awoke with my usual early morning hard-on. I went into the bathroom to relieve myself and while there grabbed a tube of KY out of my ditty bag in case I was going to get lucky with young Jimmy.

When I got back into the bed I started to cuddle to him and since we were naked my now half-hard dick was right up against the cheeks of his ass. I pushed my hips around a bit and it didn't take long for my dick to fully rise to the occasion. Jimmy felt it right away and leaned back over his shoulder to say, "Do you want me to suck you off again Bob?"

"No Jimmy, I have something else in mind. Do you remember how good it felt when I put my finger up your ass? Well, I think I would like to put the head of my cock up there to really turn you on."

"Oh God no Bob. Your dick is a lot thicker than your finger and it would hurt terribly."

"No, I don't think it would if I use some of this KY jelly on it and you are able to relax. What do you say, can I try it?"

"Oh Bob, I do want to please you but I am afraid."

"No sweat Jimmy. I'll start and if the pain gets too much just tell me and I'll stop right away. OK?"

"OK, if you promise to stop when I say so."

"Promise."

I lathered up my cock with KY and took a big gob of the cream and worked it in between the tight lips of his asshole.

"Now just relax Jimmy. It will hurt a lot more if you are all tight and wound up."

"OK, go ahead and do it."

I pushed the head of my cock against the lips of his asshole and gave a little push. All that happened was that his asshole retreated from the pressure as it resisted the penetration of my cock. I reached down and held each of his hips as I gave another push and this time I popped in a couple of inches.

"Oh Bob, that really does hurt."

"Jimmy, ease up. We have just started and you are still uptight. RELAX"

I pulled him back at me some more and went in another few inches but this time he was crying with the pain.

"Bob, I can't go on with this. It's hurting me more than I can bear," he sobbed.

"OK Jim. I won't go in any further but let's just lay like this for a little while as my cock softens."

I had no damn intention of letting my cock get soft but I thought it would comfort him if he thought the end was in sight.

I reached around and pulled his face back around to me and planted another kiss on him. He loved it and pushed one of his hands around to my neck and pulled our faces ever closer together.

"Bob, you make me feel as if you really care about me."

"And I do. Jim, it seems as if the pain has gone down. How about if I try to go in a little more?"

"OK but go slow."

I pulled his hips back as I pushed my ass forward and as I gave another thrust I was almost buried.

"Jim. I am almost all the way in you. One more push will do it."

By now he wasn't just sobbing but he was all out crying. "Ok, go ahead" he shuddered.

I gave another light push and was in him to my full seven inches. I waited a minute to see if his crying would stop or at least slow down but it didn't. I was damn sure not going to waste this penetration so I began to move ever so slowly.

"Jim, would you like it better if I pulled it out of you for a minute and let you turn over on you back so you could put your legs up in the air as I slipped it back into you. That way you could see my face as I was fucking your ass and watch me as I had my orgasm?"

He thought that would be a good idea and it didn't take very long before I was slipping back into him with one long smooth thrust. He had stopped crying when I had taken it out of him but the reinsertion brought the pain back and his tears started to flow again.